My wife is suspicious of business trips, especially big conferences. I tell her they are nothing but 2-3 days of boredom. Nine out of ten times, they are.
I attended a meeting held to bring the staff of two merged companies together for the first time. The merger impacted my team by shifting the geography of the people I managed. It was not a major concern to me since the geography shrank while the number of people increased. Besides, as a result of the merger I’d been approached by a competitor and had another job offer in hand when I boarded the plane to Miami.
The meeting included some high level executives promoting the merger and telling us how much sense it made for the employees…those who had survived the layoffs anyway. As a mid-level manager I just sat in the middle of the room mulling over my job offer. That night there was a cocktail party, dinner and more speeches. At nine o’clock the festivities ended and the partying began. Several of us went bar hopping on South Beach. The drinks were plentiful and the scenery (female) was incredible. Several others from our company found their way to the same bars which gave us all a chance to reconnect with colleagues and meet new people.
I was dancing with a young lady I’d never met before when I noticed another woman, perhaps in her late twenties or maybe early thirties, making eye contact with me. The babe I was dancing with was extremely attractive, but out of my league just based on the age difference. I thought I had a better chance with the woman by the bar. There was something familiar about her. Maybe it was wishful thinking that I knew her. Her dress was short to begin with and her dancing was forcing it to ride up her thighs to the point that the bottom of her cheeks would almost show. It was a bright red knit dress that buttoned down the front. The top two buttons were undone showing the top of her small breasts and the bottom three buttons were undone giving her room to move her legs while also showing a lot of leg…and they were gorgeous legs!
When I took a break and stood at the bar she found me and gave me a hug and greeted me by name. “You don’t remember me do you?” she asked. I admitted her face looked familiar but I couldn’t come up with her name. She gave me her name and I realized she was an administrative assistant in a market of mine that was moving to a new manager. The last time I’d seen her she was at a company party two years earlier and she was eight months pregnant and 50 pounds heavier. Her new look made her look five years younger and much hotter. Her hair color was a dark brown and nearly reached her waist. Her eyes were a gorgeous green that used to be hidden behind ugly glasses. The fifty pounds gone, she probably tipped the scales at 115 pounds with small breasts, a narrow waist and an outstanding backside that was catching more than just my attention. The envy of several guys was apparent as we chatted at the bar.
Despite not recognizing her, I knew Jennifer a little bit about her from phone calls and gossip. I knew she was in her late twenties and married with two step-kids in their mid and late teens and a two year old she shared with her 35 year old husband, Dan. At forty-six, I was almost old enough to be her father and discounted her flirting over the phone and email as just the kind of personality she had; fun loving and very outgoing, but I never interpreted it as anything more serious. I knew she had a rocky relationship with her husband, largely due to his inability to discipline his teenagers but also because she thought he cheated on her. He played in a band and she suspected he’d had more than a few flings with groupies, some just college age since they lived in a college town. That was the gossip part.
It was hard to catch up with the noise in the bar so we essentially stood at the bar shouting to each other to be heard and watching the crowd. At one point one of the guys asked if I wanted to go to the gentlemen’s club next door. I tried to decline, but Jennifer invited herself to join us and pulled me toward the door. At the club she waved dancers over to perform lap dances for the four guys at our table and at one point we had three girls dancing one-on-one with the guys, including me. That left 50 year old Paul with no one on his lap, so Jennifer hopped to her feet and started dancing in front of him. It started as a joke, but when the guys encouraged her she unbuttoned a couple more buttons – one at the top and one at the bottom of her dress. Now the top of her bra was visible and when she stuck her butt out toward Paul the bottom of her butt cheeks were just barely out of view. Paul bent down to peek up her dress and she turned around and gave him a playful slap before sitting on his lap.
A half hour later we left and headed back to the hotel. The conversation in the van was all about Jennifer (she was riding with another group). When we arrived at the hotel it was 2 AM and most of the people were catching flights home in the morning. We hung out in the bar for a short time saying good-bye as people took turns with the lobby computer to print their boarding passes. Jennifer took an empty seat next to me and gave me a flirty smile and air-kiss. The conversation about Jennifer and Paul picked up again and Jennifer just laughed it off saying alcohol was never kind to her. I told the group it was past my bedtime and headed for the elevator. Jennifer stood and asked where the ladies room was and headed in the same direction.
The elevator car arrived and I stepped in alone, but before the door closed Jennifer darted in and hit the button for the 17th floor. I was on the 21st. I asked her if she had found the ladies room and she said she’d decided she could just as soon use her own since she had an early flight and should be getting to bed. “Besides, I didn’t want to be there when the bar tab came” and she laughed. I noticed that she had buttoned up a bit, but still showed an enticing amount of skin. When the door opened at her floor, she asked me if I’d like to join her in her room. “It was so loud in the bar and there were so many people around that we never got to catch up.” When I hesitated she reminded me that I could sleep in since my flight left mid-afternoon. “You can watch TV while I pack.” It was an innocent enough invitation though my thoughts were anything but innocent.
Inside her room I was surprised what a mess she had. She had two queen beds and one was covered with clothes and there were more on the floor, including a pair of silk pajamas. Apologizing for the mess she told me, “I was running late and wanted to find the right outfit for the clubs before the van left without me. I’m much neater in my work!” She headed to the bathroom and I flipped on the TV. Five minutes later she was seated on the foot of the bed next to me asking what was on. I told her there wasn’t much this late at night. “Sure there is…porn”, and laughed at my embarrassment. I told her I should probably let her get some sleep and hit the power button on the TV remote. She told me she had to unwind a bit or she’d never get to sleep. We talked for a few minutes about our families and the changes the merger would create. She told me she would miss hearing my voice on our conference calls and I told her I’d miss talking to her as well. There were a few minutes of awkward silence and I became aware she’d noticed that I was checking out her legs as her dress had ridden up her thighs.
“So, what are you thinking?” she asked. I gave an embarassed chuckle and told her she probably wouldn’t like the answer and I should probably go so she could turn in. She asked again, “C’mon, tell me what’s going on inside that head of yours.” With a smile, I admitted I was admiring her legs and complimented her on the changes she’d made. “I’m just trying to keep my husband interested, but it’s not working” she told me. “Interested? How could he not be interested?” I asked. “He manages. I think he has other distractions to keep his attention” as she looked down at the floor and pulled her hem down a bit. “I worked hard to lose weight after our baby was born. I feel a lot better about myself, but maybe it’s too late.”
I looked at her and she turned toward me. My hand lifted her chin as I looked her in the eye and said, “You look beautiful. He’s a lucky guy.” I kissed her on the cheek and savored the scent of her perfume and the smooth skin under my lips. Our eyes met again and she thanked me for being so kind. She looked down again and said, “I’m glad you noticed my legs. I don’t have much in the boob department so my legs and butt are all I’ve got.” “They’re perfect”, I told her “You really are gorgeous.” I looked in those green eyes again and she leaned forward. Our foreheads touched and our lips were only an inch apart. She smiled at me and lifted her chin, bringing our lips together in a light kiss. That led to a longer kiss and soon her arms were around my neck and mine around her waist, pulling her closer to me. The kissing became hotter, her tongue finding mine as she lay back on the bed. I was leaning over her now, aware of her chest rising and falling as her breathing became deeper. My hands were resting on the bed but when Jennifer pulled me down to her I shifted my weight to my left elbow leaving my right hand free to explore. I started at her cheek, but quickly moved to her chest. When my hand covered her breast she let a small moan of approval escape. With thumb and forefinger I flipped one, then two buttons on her dress open and reached inside to cup her breast through her red satin bra. I could feel her nipple harden and caressed it through her bra with my thumb. Then I turned my attention to her other breast and did the same. Her kisses became more passionate as I played with her tits but still through her bra. I didn’t want to press my luck.
Jennifer broke our kiss, turning her head away from me. I let my lips travel down her neck nibbling first on her earlobe and then moving further down to just above her breasts. “What are we doing?” she whispered. I took that as a cue of disapproval and didn’t want to miss this opportunity. I moved my right hand to her knee. Without objection I released a button, then another and moved my hand up her thigh. She purred in my ear “oh my” as I pushed higher. Another two buttons and her dress was open to her waist. I took a second to peek and noticed she was wearing a pair of tiny panties that matched the red satin bra, and that was my mistake. Just the small break from my lips and tongue on her neck and chest and knowing I was looking at her made her self-conscious. She pushed away and sat up. “We should stop. We’re both married and this is wrong” she protested. “I shouldn’t have asked you to come to my room” she said and looked toward the door. “Probably not if you really thought we’d just watch TV and talk” I told her. “But I think you knew exactly what would happen if we were alone. I think we both wanted this to happen.”
Jennifer looked down at her legs dangling off the end of the bed. She looked confused. “I wasn’t thinking. I saw you in the club and started fantasizing about you. I wondered how I could get you to my room, maybe into my bed, but I didn’t mean for it to happen” she said. I put my hand on her knee again and started sliding it up her thigh. “It’s not a fantasy, but I’ll leave if you want me to” I said very softly. Jennifer pushed away and moved higher on the bed, her legs no longer dangling over the end. My hand found her calf and I started to move it higher, sliding up her bare thigh. I reached her panties and felt the dampness there that told me she wanted me. She closed her eyes and turned her head away. “If you think you’d feel guilty about it tomorrow, then I should go.” Jennifer looked back at me, our lips inches apart and my fingers easing inside the top of her panties. She grabbed my wrist and just whispered “No…please stop” but it was too late. My fingertip slipped between her lips. I felt how wet and slick she was. She gasped and clenched her thighs around my wrist. I slid my finger deeper inside her. She moaned and relaxed her thighs enough to move her hand over mine. Instead of removing it she pushed it deeper.
“We have to stop…this is wrong” she whispered but she pushed my hand tight against her pussy and I slid a second finger inside her. I leaned over her, whispering in her ear, “You don’t want to stop. You want my hands on you. I can feel it. You want my lips and tongue on your nipples…and you want my fingers inside you. You don’t want to stop any more than I do.” I kissed her neck and continued fingering her, then reached behind with my left hand and pulled her dress off her shoulders and unhooked her bra (no easy trick for a righty). I didn’t dare remove my hand from between her thighs, but I pulled the bra strap from one shoulder. She took over and slid it down and off her arms then laid back on the bed with her arms stretched out above her head. It was her surrender, or so I hoped.
I moved to her nipples and sucked and nibbled them as she arched her back off the bed. “God, Jack, what are you doing to me? I’m married…and this is so wrong…but it feels so good and I want you so bad.” I moved to nuzzle her neck gently at the same time I shoved her panties down to the top of her thighs. I bent over her and sucked her nipples between my lips. She closed her eyes and moaned “Oh god that feels so good.” My thumb caressed her clit and her left hand covered my right hand and pressed it hard into her pussy. “Oh my god, don’t stop. Please don’t stop” she told me as I fingered her wet slit.
We continued like this for several minutes, my fingers sliding in and out of her as I rubbed her clit, bringing her close to climax. At the same time I alternated between kissing her and sucking her nipples which seemed to be very sensitive and hardwired to her pussy. I knew I needed to take a break and undress, but I was worried she’d panic again. She helped out by unbuttoning my shirt and slipping one hand inside to rub my chest. Her other hand gripped the tricep of my left arm which was supporting my weight above her. She lifted her knees toward her chest and I pulled her panties off. When she lowered her knees her legs parted for me to allow better manipulation of her pussy. Her hands unbuttoned the cuffs of my shirt and I tugged it off quickly. Then I made another miscalculation. When my hand left her pussy she regained her resolve. She pulled away from me and moved across the bed leaving me sitting alone. She was breathing heavy, her legs tucked under her and covering her breasts with one arm as she pulled her dressed closed around her with the other. I resigned myself that it was wrong for her and retrieved my shirt from the floor. I slipped it over my shoulders and headed toward the door.
“Wait” she said. She held the dress around her and followed me to the door. “I’m sorry, Jack. I want to, but it’s wrong.” I just smiled at her and kissed her cheek. “I know it’s wrong, Jennifer. I’m married too, but you asked me up here and I came, and I knew what we were getting into and so did you. You wanted me make love to you, but, hey, a woman can change her mind” I told her and turned toward the door and opened it. She grabbed my wrist and stopped me, then stepped between me and the door and pushed it shut. She looked down at her feet, then in my eyes and asked me, “This will be our secret?” I just nodded. She released my wrist and dropped the robe from her shoulders and tossed it to the bed. It was the best view I’d had of her. “You look beautiful. Just gorgeous” I told her. She smiled and sheepishly reached out with both hands and took mine in hers. “Come with me” she said and led me to the bed, pulled down the sheets then turned and started removing my shirt again. She reached for my belt and zipper. I kicked off my shoes and removed my slacks and socks. My cock was making a tent of my boxer briefs and Jennifer wrapped her hand around it.
She breathed a deep sigh and looked at me saying, “I hope you know what you’re in for. In bed I’m not very well-mannered.” I looked at her quizzically and she laughed. “Let’s put it this way, it’s been a long time since I’ve sucked a cock. Dan hasn’t let me near his lately. And I haven’t been really fucked for over a year. I mean really f-u-c-k-e-d. So you better have some staying power, baby because if we’re going to do this we’re not doing it half-assed. I’m going to fuck you all night.” With that said, she dropped to her knees and pulled my briefs to the floor, wrapped her hand around my shaft and pumped it a couple times, then looked up at me and giggled before she took my cock in her mouth and sucked me.
It was sublime. To say she was a good cocksucker is like saying a first chair concert violinist can play the fiddle. I had my hands buried in her hair to back her off when I was close to coming but it wasn’t necessary. For a girl out of practice, she knew exactly how far to push me before letting up. When I finally told her not to stop she looked up at me and smiled, “Shoe on the other foot now?” She released my stiff shaft and moved to the bed.
Lying back she struck a Penthouse model’s pose with her arms stretched out above her head, one knee bent and the other stretched out, her thighs slightly apart. “Get over here on the bed baby and lick my pussy.” I did as I was told. Soon she had her thighs squeezing my head and holding me tight to her sex. She told me exactly what she wanted, frequently between clenched teeth and in very blunt terms. “Lick all the way up, baby. Start down by my asshole and lick all the way to my clit. Now suck my clit. Suck it” was just an example. I flicked my tongue over her lips and clit, sucked her clit between my lips until she was begging me to let her cum. I tried to back off to let her rest and come down a bit, to make it last, but she just grabbed my hair and pulled me back to her pussy. I went down again, this time keeping it going until she exploded in orgasm.
She opened her eyes again when I spread her legs and moved between them. She reached for my throbbing cock, looking me in the eye as she told me, “I’ve wanted this for so long. I’ve wanted you ever since that party two years ago. (I was above her with her now.) You looked so good in that tuxedo. (She rubbed the head of my cock up and down her slit as she spoke.) I had to dance in wet panties all night. (Her juices were wetting the head of my cock.) I wanted you to take me back to your room and fuck me all night.” (With that she put the head of my cock between her lips and used her legs to pull me forward, taking my cock deep inside her.) “Take it slow and let me get used to you. Ahhh, that’s it. Now you’re in my room (thrust)…in my bed (thrust)…and your hard cock’s (thrust) in my wet pussy (thrust)…and you’re fucking me (thrust). Fuck me, baby.” I started moving inside her faster and harder. I felt her legs wrap around me, pulling me deep inside her, then letting me pull back and plunge into her again. It was the hottest fuck of my life, even though it didn’t last long. Just five minutes later she was pulling my hair and squeezing me with her legs as I grabbed both cheeks of her ass and plunged into her again and again before exploding.
Our recess didn’t last long. Within fifteen minutes she was going down on me again and got me hard pretty quickly. Her fingers were playing with her pussy as she sucked me. I could see she enjoyed it as she closed her eyes and moaned around my cock. Pulling my shaft from her mouth and rubbing the tip against her nipples she looked at me and smiled. I asked her if she liked pleasuring herself and she reminded me that it was about all the action she’d gotten since her son was born. Then she spun around and got on her hands and knees facing away from me and looked back with a wicked grin, “Let’s see if you can last longer this time. You can fuck me like this while I play with my clit and I’ll show you what I mean about not being very ladylike.”
I moved her to the edge of the bed so I could stand on the floor and get a little more leverage. She loved the idea. I slid my cock in her from behind and started pumping it into her pussy, hard. My balls were bumping her hand as she fingered her clit and soon there was a very audible sound of skin on skin with my hips slapping against her tight round ass. She talked, whimpered, moaned and begged for me to fuck her, to make her cum. She tossed her long hair and glared back at me over her shoulder urging me to fuck her harder. I was sure anyone in the hallway or neighboring rooms could hear her but was also sure if it was a male, and maybe even a female, they’d be jealous as hell about what was going on out of view. Eventually Jennifer came all over my cock, her juices running down her legs, but she didn’t miss a beat. She turned around and had me lay on my back, then mounted me and rode me until I came again, deep inside her. Just before I did she bent over and whispered in my ear, “I want you to remember this night. I want to be the best you’ve ever had. I want you to think about me when you’re in bed with your wife and think of me every time, no matter who you’re with.” She lay beside me and we fell asleep in her bed.
Jennifer had an early flight and had to get up at 4:30am to catch her plane. I woke to the sound of running water and found her just out of the shower. I boosted her up onto the vanity and got down between her thighs to get her juices flowing. “Oh, god Jack, you’re going to make me miss my plane”. I stood between her thighs and slipped inside her. It was a great view in the mirror behind her; her cute little butt on the edge of the sink, undullating her hips in time with my thrusts deep inside her, her long hair hanging wet down her back moving gently as I moved inside her. Her arms were wrapped around my neck with her head on my shoulder and her lips kissing my neck. She was quietly whispering in my ear and when I understood what she was saying I felt a little guilty for the first time. Over and over she whispered “love me…please love me…love me…please love me…” but as our pace picked up, her chant changed to “fuck me….please fuck me harder…fuck me baby…fuck me” until I came deep inside her one last time as her body stiffened and her legs held me tight between her thighs.
I had a rental car and drove her to the airport. We shared a long kiss out of sight of other passengers and vowed to keep in touch. As she walked away she turned and mouthed the words “thank you”, blew me a kiss and darted inside dragging her rollerbag.
I took the new job and it takes me to Jennifer’s city once in a while, but I haven’t tried to contact her. She was right. I think of her every time and I don’t want to spoil it.
Gerald is that type of best friend, where no matter how much time has passed between visits or talks, you can pick up right where you left off, without missing a beat. So, when he was finally able to visit us, we fell into our natural rhythm of stories and humor, heavy on the sexual innuendo with my wife, Christie.
In retrospect, it’s easy to see how we were all hoping something would happen. Gerald… recently breaking up from a long-term relationship and looking for some fun… and us, looking for the right moment and person to start experimenting…
Our first collective attempt isn’t necessarily noteworthy… it was rushed, almost hurried in that effort to cross that unspoken barrier…
The next night, though, is worth a story…
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A few months ago I wrote about an affair I had with a woman I worked with named Mary. We moved quickly from a contentious relationship with her to one that was pure lust. It started when she offered me a kiss as reward for helping her close a sale and progressed to several quick interludes and one long, lazy afternoon before she moved away for a new job.
We were a good professional team and I continued to enjoy success and receive recognition and offers of promotion but my wife and I had kids in school and didn’t want to move. I also noticed that several peers moved up the ladder only to be pushed off by someone a little more adept at climbing. My clients liked me and were good to me leaving me plenty of time for golf and fishing. Besides, there was a young secretary at one of the companies I called on who was anxious to spread her legs for anybody, male or female, who could help her career and I was hoping I could find a way to help her climb her own ladder.
A year after Mary had moved we were scheduled to attend a conference where I was scheduled to lead a panel discussion on how to use social media to acquire new clients and strengthen relationship with current clients. We were scheduled to present just before the end of the first day and I’d been unable to connect with Mary all day. I saw her at the conference, but it was obvious she was avoiding me, choosing instead to flirt with men who could give her a boost on the corporate ladder.
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Even though we swing, my wife (Paola) had always been very bashful and unnecessarily self conscious. She stands 5’4”, weighs 110 pounds and has perfect tits with protruding nipples slightly larger than pencil erasers. The nipples were the cause of her self consciousness and she flatly refused to go anywhere without a bra or other nipple shield. Everyone we have been with has told her that her concerns are unfounded, but she was steadfast and refused to change. We frequently travel together and, in efforts to boost her confidence, I have encouraged her to go braless and pickup someone for some fun. She still refused to give in.
For our most recent vacation, she left two weeks before me and went on a cruise with her parents. After their cruise, I was to meet them in Paris where we would stay until her parents returned to Chile and we traveled to Germany for our two weeks together. Before she left, I encouraged her to be naughty, but fill me in when I arrived.
Unfortunately (maybe) I was delayed three days and her parents had to return home just a few hours before I landed. As I was walking towards baggage claims, I noticed a sexy woman with a VERY short and shear white dress. I did not know if my eyes were playing tricks or not, but I could have sworn I could see pussy lips, and the lines appeared to be tan lines, not panty lines. As she turned, my gaze fell upon a braless and perfect rack. It took several seconds before I realized those titties were coming towards me. I forced myself to look up, after a second downward glance and confirmation that I had seen pussy lips, and realized Paola had finally given in and was doing as I had asked. And from the look on her face she was enjoying it more than I had ever imagined.
The greyhound bus, aka the loser cruiser. I think we can all think of a time when we spent a uncomfortable ride on one regretting not spending the extra money to fly and actually feel like a human and not a sardine crammed in a tin. Well this trip was no different, I was looking forward to a 13 hour red eye bus ride up north to visit my girlfriend and the only thing I could think about when I watched the bus pull up to the bus stop was pray it wasn’t overly crowded. Sure enough i found myself crammed into a seat next to a fat guy with horrible BO and to boot seemed to have an affliliation with magically materializing a seemingly endless supply of cheese burgers out of his bag. The only consoling point I had during the trip was the opportunity to chat with a 30 something woman sitting across the isle. She wasn’t really anything too special, but when sitting next to jabba the hut, even a small ray of light starts to look like the sun.
We had a 3 hour lay over in a smallish city and sure enough I found myself in a sleezy bar having a drink with this woman. She revealed to me she was a stripper who was heading up north to her next stop to perform. I was rather incredulous but sure enough she produced a poster and a couple of fridge magnets to validate her story. After a couple more drinks our conversation turned to sex, our favorite positions, and even to my penis size. I thought it was relaively harmless and faced with a 8 hour overnight ride to the next lay over, I figured there was no harm in getting a little drunk before I embarked. She seemed to have the same idea, and by the time we made our way back to the terminal, we were both feeling rather tipsy.
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Natalie and I had gotten caught by her boss at the tux shop having sex in a dressing room. In an odd twist of fate, that encounter led to me taking her boss, Monica, to a formal event and then dating her for the past several weeks. During that time, Monica and I showed equally poor judgment by letting Monica give me a blowjob in a dressing room while Natalie and another associate were helping a wedding party pick out tuxedos for the groomsmen. I made a little too much noise and saw Natalie peeking through a door as Monica was going down on me.
That led to another unexpected meeting. In the process of fitting me for my tux, Natalie had asked where I worked and found out I had my own firm. She also found out I was looking for a new assistant. A few weeks after I started dating Monica, Natalie called and asked me for an interview. It seemed best not to tell Monica about the call or meet Natalie at my office. I knew hiring her would be the end of my relationship with Monica and I certainly didn’t want to create any problems in her marriage.
Still, we needed some privacy in case our previous encounter came up. I booked us a table at a nice café in the lobby of the Hilton where I knew the manager and he gave us a small table in a quiet corner. Natalie showed up on time in a business suit, but the skirt was too short, the blouse was too sheer and her heels were definitely not what a woman on her feet all day would wear. She sat next to me like a lover would rather than across the table. We covered the pleasantries then ordered lunch. While we ate we talked about the job. She didn’t seem that interested. She played with her food but didn’t eat much. I realized she was very nervous.
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I wrote earlier about a quick fling I had with a cute little salesgirl at the tuxedo shop. After getting caught by the owner of the shop in mid-climax, I faced the unwelcome task of going back to see the owner for my final fitting and to pick up the suit.
Walking into the store just before closing, she barely acknowledged me as she helped a wedding party get organized and out the door with their duds. One more client came in after me to return his tux, so she told me to wait in the second dressing room on the right. “You can strip and I’ll get your tux from the back and bring it to your dressing room.” I found the use of the word “strip” a bit intimidating, but sexy. The lights in the front of the store switched off and I assumed she locked up. I heard her walk past the dressing room as I stepped out of my slacks and stood waiting for the moment of truth.
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Black Tie Event
My wife moved out six months ago. I poured myself into work to occupy my time and the result was great for my career, but bad for my social life and my health. Now I’m nothing special. I just celebrated my 50th birthday, have a bit of gray hair peeking through the brown hair I was born with, blue eyes and a crooked smile that my wife found adorable. After getting a lecture from my doctor, I started spending less time at my desk in more at the gym. I’m a bit over six feet tall and down 40 pounds to 210 and I continue to work out several times a week to keep the spare tire off. He also put me on a daily regimen of Cialis to keep me in the game, even though I had no game and no one to play with.
I had a black tie dinner coming up in a couple weeks and needed a tuxedo. I went to the local tux shop late on a Sunday afternoon for a fitting, close to closing time, and was pleased to find an attractive young woman behind the counter. She was in her late 20s, about five feet, four inches tall with long dark hair with a bit of curl spilling down past her shoulders. She was wearing a sheer flowered top with a small sweater that didn’t hide much and tight black pants that showed off a shapely backside. I was busy checking her out whenever she wasn’t paying attention and was caught a couple times admiring the cleavage and slopes of the top of her breasts when she wasn’t looking. When she bent over to retrieve a spiral notebook with pictures and options to consider I noticed a bit of pink thong peeking out above the waistline at the back of her slacks. She caught me looking and gave me a sly, knowing smile that let me know I was busted.
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My son’s babysitter is an 18-year-old senior in high school, 5-foot-6, thin, curvy, with blue eyes and long golden blonde hair. But she’s not the one this story is about. She’s been our baby sitter for two years, so instead of viewing her as sexy, I still see her as the cute kid who babysits.
Her mom, Alice, on the other hand is a knockout. Same height as her daughter, a tad bit heavier, but with nice curves, fine ass, great looking 36C breasts, short blonde hair and sparkling blue eyes. Our families are friendly and she has a great personality. One time she jokingly introduced me to her husband as her boyfriend. In front of my wife, I jokingly called her my sugar momma. However our friendship went to a whole new level recently.
Alice had joined my wife Kara and I for lunch one day . We usually greet eachother with hugs and I told her she looked like she could use one today and her hug felt a little closer and a little longer than usual.She was a little upset as she told us about her rough morning and how she can’t stand her new co-worker. Then she dropped a bombshell on us and said “Kara, I feel really guilty about asking this. But would it be possible if I borrowed Gary for an hour or two?”
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I came home from a multi-day road trip on a mid afternoon. My wife was waiting on me and as usual I wanted to decompress with a quick shower and a change of clothes. She had just gotten back from Yoga, had a bath robe on and said she’d meet me down stairs with a drink when I got done. I kissed her before she left smelling her sweet perfume along her neck.
I entered the shower with visions already dancing by her simply wearing a bath robe and what may be underneath as well as the promise of a nice drink to match. My cock was already getting hard at the thought of our next steps and after a quick shower I headed downstairs to her in the living room where she had the stereo on and playing some great sensual music which only added to the anticipation of what might be to come.
I only had a bath towel wrapped around my waist as I headed downstairs but based upon what I saw from her partially open robe I was probably over dressed. As I approached her she pulled the robe back off her shoulders and kissed me passionately asking what took me so long to shower. I fumbled for a response as I was focused on her and moved in to meet her kiss and pushed her robe further down and saw that she was gift wrapped in a beautiful black bra and barely there panty with a chain front guarding the prize that I hoped for. Her pussy was beautifully trimmed and the panties perfectly framed the masterpiece between her sweet thighs. My cock leapt at the thought of taking her immediately and fucking her with abandon, but she soon made it clear this would be on her terms.
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